The Dating Diaries: Sara and Jeremy

Sara is a 24 year old marketing coordinator who enjoys reading, cooking, and attending events in the city. Her dating life consists of a series of dates, usually in the summer, that fizzle down soon after. She describes herself as stylish, driven, and fun, but most of all, kind-hearted and giving. She asks “Where are the handsome, smart, nice men?”

It was a couple days before Valentine’s Day and the handsome phone-booth guy from the mall asked me out when I went to look at a new case for my iPhone. I was trying to ignore his deep blue eyes flirting with me from behind his kiosk, but he had already said hello a few times since his store was so close to the food court, part of my daily Pam’s coffee route.

I hesitantly agreed to have an official first date on this dreaded V-day, but since it was a Friday art crawl, company didn’t seem so bad. Plus he was annoyingly handsome, so it was frustrating justifying saying no.

We started out at the Jackson Square theatre (really romantic, idiot) to see a (terrible) rom com. Kudos to him for choosing a movie that’s more my style, but minus some points for sneaking in a flask like a high schooler. I guess that’s what people do in empty theatres in Hamilton. I didn’t even know what a Jackson Square was until I moved here a year ago.

The sappy true love rom-com film was handled with enthusiasm, followed by munching on leftover popcorn as we perused up along James Street North. We browsed through the art galleries before ending up at Baltimore House for a make-out session on antique furniture in the back of the bar.

A highlight of the date was when we stopped at Centre3 and participated in one of their exhibits: writing to someone who you love the most on a postcard on the wall, a good way to bond fairly quickly and see how someone reacts to the L word. Spoiler alert: guys don’t like to talk about it. But when I pressured him to participate, my name ended up on the paper (gasp).

Verdict: We dated for a month after that and then he dumped me. Months later, we tried again for 7 months. And then he dumped me again. We tried again three months later, and three months after that, until I quit him like a bad habit. At least it wasn’t a one-hit wonder, but surely not husband material. Next time I’ll know better before taking stray tech nerds home from Jackson Square.